Gender is a salient feature of identity that is rarely questioned in our physical encounters. We are usually not confused about a person’s gender—generally it’s male or female. However, as the adoption of computer-mediated communication increases, our social reliance on these technologies has made gender easily disguised online. And yet, the phenomenon of gender deception has not been fully investigated. This study adopts a path analysis to examine interconnected cognitive factors that impact online users’ ability to deceive—and detect deception—regarding gender. An asynchronous online game was developed to simulate situations where males were incentivized to communicate like females, and females were incentivized to communicate like males. Twelve hypotheses were tested using path analysis, which resulted in our realization that an actor’s true gender can affect the motivation to deceive; males tend to have higher self-efficacy beliefs in gender deception, and females tend to have a higher success rate in detecting gender deception. Our research suggests that the gender of the message recipient could be a significant factor in uncovering gender deception.